Synthesis of 3-Sulfonyloxypyridines: Oxidative Ring Expansion of α-Furyl­sulfonamides and N→O Sulfonyl Transfer

Robert Hodgson; Andrew Kennedy; Adam Nelson; Alexis Perry

doi:10.1055/s-2007-973875

LETTER

Synthesis of 3-Sulfonyloxypyridines: Oxidative Ring Expansion of α-Furylsulfonamides and N→O Sulfonyl Transfer

Robert Hodgson^a, Andrew Kennedy^b, Adam Nelson*^a, Alexis Perry*^a
^a Department of Chemistry, University of Leeds, Leeds, LS2 9JT, UK
Fax: +44(113)3436565; e-Mail: a.s.nelson@leeds.ac.uk; e-Mail: oldralph@hotmail.co.uk;
^b Synthetic Chemistry, Chemical Development, GlaxoSmithKline, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK

Abstract

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Abstract

N-Sulfonyl pyridinones derived from α-furylsulfonamides may be aromatised with concomitant N→O sulfonyl transfer to produce 3-sulfonyloxypyridines.

Key words

furans - pyridines - rearrangements - ring expansion - sulfonamides

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Synthesis of 3-Sulfonyloxypyridines: Oxidative Ring Expansion of α-Furyl­sulfonamides and N→O Sulfonyl Transfer

Synthesis of 3-Sulfonyloxypyridines: Oxidative Ring Expansion of α-Furylsulfonamides and N→O Sulfonyl Transfer